the bossbabe podcast - 227. How To Leave Your 9-to-5 with Jenna Kutcher

Episode Date: June 28, 2022

There's no such thing as “supposed to” – especially when it comes to your life + business. In this week’s episode, Jenna Kutcher is telling us all about the moment she realized she couldn’t stay at her nine-to-five, how she started her first side hustle + what she did to build the life she (literally) dreamed of.  Plus – she’s unpacking why trusting yourself and taking imperfect action is the secret key to your success. You’re not going to want to miss this. Listen now! Highlights: Why seeing her boss’s family photo was Jenna Kutcher’s wake-up moment What buying a pair of new jeans has to do with your success in life + business How to start trusting yourself again + why imperfect action is the key to results The secret about side-hustles that nobody tells you Links: Read the amazing new book — how are you, really? The Expert Series — Grab Jenna’s brand NEW course + FULL bonus suite for FREE! Goal Digger Podcast — Tune in to Jenna’s live-workshop style podcast for more business building inspo! The Société — Join our private, online community of female entrepreneurs where you can connect, build and grow. How To Make $10k In The Next 30 Days – What if making $10k didn’t have to feel impossible? And what if you had a clear + proven path forward to grow your business after that? During this 90-minute training, bossbabe President, Danielle Canty is taking the guesswork out of how to make more money – whether you’re looking to start your side hustle or grow your business. Follow: bossbabe: @bossbabe.inc Danielle Canty: @daniellecanty Natalie Ellis: @iamnatalie Instagram: @jennakutcher Twitter: @jennakutcher YouTube: bossbabe: subscribe

Momentum is a powerful thing, but you can also generate momentum again, right? Like you got going once, you got the ball rolling, like you can slow it down a little bit and it's going to be okay. And I think we worry like, if I slow down, am I going to be irrelevant? Am I not going to be able to get started again? Are people going to forget about me? Am I going to miss my big break? Forgetting again, you know, what has gotten us here will carry us forward.

A boss babe is unapologetically ambitious and paves the way for herself and other women to rise, keep going and fighting on. She is on a mission to be her best self in all areas. It's just believing in yourself, confidently stepping outside her comfort zone to create her own vision of success. Hello, and welcome to the Boss Babe podcast, the place where we share with you the real behind scenes of building successful businesses, achieving big performance and learning how to balance it all. I'm Danielle Canty, as you guys I'm sure know now, I am the co-founder of Boss Babe and your host for today's episode. So I know firsthand that sometimes life doesn't really turn out how you think it is. And when

you're of a certain age, you think there are these supposed to's in your life. You're supposed to get married by, let's say, the age of 25. You're supposed to have children. You're supposed to marry the love of your life and meet that soulmate the first time. And you're supposed to have this incredible career or this growing six-figure business. But I'm actually really glad that I can say and break this to you if it's news to you, but there's no such thing as supposed to, especially when it comes to your life. And that's what Jenna and I are talking about in this week's episode. This is one of the most empowering episodes that I feel like we've done for a little while, although we literally have such phenomenal guests in here. But it's

really about taking control of your life and deciding, look, do you want a nine to five or don't you want the nine to five? It's okay if you don't. And here are some things that you can do about it. Jenna is an author and host of popular podcast, Gold Digger. You might've heard her on that. And we talk about business and entrepreneurship and how she made that actual transition in her own life.

She was in a corporate job. I actually didn't know this about her story and you probably didn't know either. Like she had this corporate job and she transitioned. She bought this camera for $300 on Craigslist and turned that into a hugely, wildly successful seven figure business. In this episode, we talk about what that reframe looked like. So if you are sat here listening going, look, I have a nine to five. I don't know how to leave it. This episode is for you. We talk about a reframe on our perspectives each

because we've both done it. What that looked like, some of the transitions that we had to make, some of the challenges that we had to overcome and really just got into the nitty gritty. So if you are in this position, you are not alone and it truly is possible for you. And to be honest, that's why we created this society as well, our membership for female

entrepreneurs. So please, please don't give up on your dream if you want to be leaving your nine to five. And if you want an extra little boost, a little push, first of all, listen to this episode, but also sign up in the description for a training that I am doing, teaching you how to do this exact thing, how to start a business, how am doing, teaching you how to do this exact thing, how to start a business, how to grow a business and how to replace your full-time income, your part-time income so that you can have that flexibility so that you can follow the purpose and create a business that lights you up. And you can actually create that financial control

to grow your own personal wealth exponentially. So I'm really excited for you to join in. As you're going to hear, start by chatting to Jenna about one real question. One question that we often answer very flippantly. Yeah, we're good. But how are you really? Like if you think about it, how are you really? That's where we're going to start on this episode. So I hope you enjoy and I also look forward to seeing you on my training welcome Jenna Kutcher back on the Boss Babe podcast oh it's such an honor and it's so fun to get to come back on shows because we already got past a lot of the you know the initial bio now we get to dive deep I know right this is actually one thing that I want to change

yeah in our boss babe lineup yeah to get people back on the show more yeah because it is like I know you more I know the questions to I'm not like you know I need to go deep I don't know how to get under your skin now yes let's do it I love. I love it. So, okay. As much as I know you, I was pretty shocked reading your book because I was like, wait, what? Jenna wasn't always a photographer because I had known you from being a photographer that had really taken that online, teaching women how to kind of pursue their dreams and take action on them. And then when you sent me your book to read, and I was reading the first chapter and I'm like,

Jenna had an office job? Wait, I did not know this. Isn't that wild? You know, it feels like a lifetime ago. It was 11 years ago now. And right out of college, I got a job. And I was so excited because I literally remember my last semester of school, I took like a personal finance class and I was like, I have a salary. I have a 401k.

I have made it. Especially being from the Midwest, that security is such a huge accomplishment. My parents both worked the same job for decades, and that was just kind of the path that you go on. I remember starting that job. I commuted almost an hour each way. I worked. The expectation was 10 hours a day. No one really left. Your work was never done. And I enjoyed the challenge because there was a big focus on leadership and feedback, which I really did appreciate in the structure of the corporation. But I was a glorified hustler there. I worked in retail, so I was in a Target store running HR, but you also had to be out on the floor in the back room, stocking the shelves. I had to bring the garbage to the dumpster.

So it's like, yeah, you have the office job and the office responsibilities on top of running a multi-million dollar store. I also had to wear red and khaki, which we won't get into, but I hate red and khaki. It's like haunting you to this day. Truly. Truly. So what I want to talk about on this podcast is we have a lot of ambitious women listening. And a lot of people have, just like you and I, started on that career path.

You know, we're like, I mean, I've told my story enough times where I was like, right, college, get a job. Oh, I'm unhappy doing this job. Shit, I've just paid all this money in college fees and now I don't want to do it anymore. Like, what the hell am I going to do? I feel like a lot of women are in this position, you know, a lot of women are looking to like leave their jobs and start their side hustles. So I really want you to just share your story and the facts of like, because you've actually been kind of through a few job changes if we look at it that way, from having the office job to starting photography to now having a fully online business. So I want to just hear a little bit more about what motivated you and how you actually started making those changes.

Yeah. Because it's freaking daunting. Super daunting. So my wake up moment was when I went into an office with my boss, who was a woman. And I noticed that she had this picture in her office and it was her two children. And she kind of brought them up, but she was one of the women who I worked with, who kind of kept career and motherhood very separate. And she was kind of two different people. Right. And I remember saying like, look at those little kids. Oh my gosh, you're so cute.

They're these little blondies. And she goes, you know, if I'm lucky, I get home in time for bath time and bedtime each night, if I'm lucky. And I realized like she's working hard to pay someone else to raise her children. And even at the time I didn't want kids. Like I was very clear. I didn't want children. But I remember in that meeting, she like presented me a five-year plan without asking, what do you want for your, so she's like, we sat down, we've mapped it all out. You're going to move up and up and up. You'll make more money, but you'll have more responsibility. And I was like, no one asked me if I wanted this. And it was a massive wake-up call because I recognized that I was on this path that literally someone else was planning for me. And I went back to my office that day and I still have this picture

in my world because it really transformed me. But it was a picture of Drew and I at like a college party in this red picture frame. I remember looking at him and thinking about how she must look at her kids and like long for them and wonder, is this worth it? And I looked at that picture of Drew and I, and I was like, do I want to spend my days working at a desk, looking at the person I love in a picture frame? Or do I want to figure out a way that I can spend time with them? And for a lot of people right now, leaving the workforce or having this desire, a lot of times we're like, I don't know what my purpose is. I don't know what I'm passionate about. I know for me in the corporate setting, I felt the least creative I've ever felt in my life.

I couldn't generate ideas. I couldn't hold visions. I was burnt out to a crisp where I was like, I don't know what I want, but I know what I don't want. And that really propelled me forward of like, how do I create freedom? How do I build something? How do I enjoy life again? And at the time, Drew and I were planning our wedding and I had bought a camera. I've always loved documenting things. I was the kid that would go to prom with the wind-up Kodak cameras and take all the pictures and look forward to picking up the photos at Walgreens. And I bought a camera. I started feeling creative again. And I was extremely passionate about photography and learning it, but I also had a lot of doubts.

I never went to art school. I never took a photography class in my life, but I knew business. And that was when I started to figure out, whoa, I think I can make money doing this. I remember my brother-in-law and sister-in-law got married in Jamaica and I brought along my fancy new camera and I was all in. I was hanging her dress in trees. I was putting their rings on her flip-flops. Like I was like, I'm going to do these pictures for them. Like I was like, I don't trust the resort photographer. Don't worry, I have a camera from Craigslist.

And so it was a first spark of like, wait, if I'm going to go all in, I'm going to do it. And I actually really enjoyed it. And after I posted it on Facebook titled my first photography project, which got 12 likes and one comment, I starting a business. And like you said, I've had a lot of different almost careers in the decade of entrepreneurship. I've gone in a lot of different directions. I've tried a lot of different things. And every time I am propelled by figuring out like what is, what feels in

alignment, but like, how do I not abandon what's already working? I love that. That's so key. And I just want to focus on that point that you just said that, like, how do I not abandon what's already working? Because I think that's really important to emphasize because a lot of people when they're in this position where they're like, I want to get out of this, but I don't really know how. I think that's something that really comes up. So how did you explore that for yourself? Yeah. Every single thing I've done, and let me list them off because I don't even think people know all of them. So I was a photographer. I started a watercolor print shop. Wait, what? Yep. Okay, no, I did not know these.

Yep. I launched my podcast. I did influencer partnerships. I have Airbnbs. I've created online courses, had a mastermind. I've done all of these things, most of which I'm not still doing to this day. Every single one of them started as a side hustle. And it was intentional. And what I love about that,

and what I feel like is forgotten, especially among women entrepreneur, is it feels like we're in this polarizing situation where you either have to be all in as a CEO, or you have just a cute little hobby. And I'm like, side hustlers unite because there's something so beautiful about leveraging what's already working or having the security and the stability from something that

you can do and know that you can make money doing while you explore and experiment and adventure. And the beautiful thing about that is every side hustle has started out as a trial. There's no stress. There's no like success or failure. There's no urgency. There's no scarcity. And so everything I've done and continue to do starts as like, let's just see how this feels. I could not agree more on this point. Like I feel like this is the all or nothing world that we live in right now. And I just don't think that's the best way to like start your business. I think, you know, if you can work out a way to keep your nine till five and get your business off the ground is the best way because I've shared with you and we shared

this in a conversation that we did for your book was that, well, hang on a minute. You don't know like what is actually going to work. Like you need to find product market fit. And if you abandon everything or your salary or your income and your job to go fully into this, you're on a deadline. And that is scary. It took me two years from declaring I wanted to transition

from being a chiropractor and saying I wanted an online business. It took me two years to really find what worked and what didn't. Like just like you, I was like, okay, I'll start an Amazon store. I'll do network marketing. I'll do some like one-to-one business coaching because I can talk about brick and mortar businesses. Like so many things I tried and it was all like trial and error.

So I think like permission to like, I mean, women are great at multitasking anyway. Like permission to multitask your roles and responsibilities more. Absolutely. You know, even as you're speaking, I'm like thinking about things that I've tried and failed. Like I did senior photos for one year and I was like, this is not for me. Like things like that. And it's like, I look at that as like a really deep place to like try and then be like, oh, nevermind. I changed my mind. And I think you and I have talked about this a lot in just private conversations too. Women are so afraid

to change your minds or to like, say like, hey, I did this and like, it didn't work or it didn't feel like I thought it would feel. I'm going to try something different. And it's like, we almost like back ourselves into corners and think that like, if we said this thing once, clearly 10 years from now, somebody's going to ask me how that thing went. And if I'm not doing it, I'm a failure. And it's crazy because it's like, everyone is so doing that in their own lives. Like our heads are so down in our own lives. No one's paying attention to you. No one cares if you try something and it doesn't work out. And we become so afraid of like standing at a starting line again. That is very, very true. And I want to ask you, like, what is your advice to people like that? Because I think that's a real problem. People being like, oh, I don't, I feel like people are

scared to get things wrong, maybe. Oh, 100%. Scared to like, oh, well, I said I was going to do this. Like you said, 10 years ago and now I don't want to do it anymore. Like we forget that we're allowed to change. Oh my gosh. Yes. There is a chapter in my book and it starts off and it talks about like when we used to sign yearbooks and we would be like, never change. And at the end of the chapter, I'm like, if I could sign people's yearbooks now, I would say like like I can't wait to watch you change and grow and evolve I can't wait to see who you'd become oh my god you know what I've just realized what there used to be this thing like if anyone got in like ex-boyfriends or like partners at times like oh you're changing yes that must be a bad thing yes damn right I'm changing I'm growing up and

I'm getting older like learning more learning. More embarrassing not to change. And I was like, that was said in such a negative way. Like, oh, you've changed. Yes. Yes, I have changed. Yes. Isn't that amazing? It's been 14 years. Yes.

And here's the thing too, is it's like, we're so afraid to contradict ourselves or change our minds that we often stay stuck. It's like the same reason that we hold on to like our genes from high school or the same reason why we like finish the degree, even though we know we hate the destination of the degree. And it's like, we are so worried about like, have I wasted time that we don't care that we're still wasting that time moving forward. And so when it comes to change and stuff, like I love contradicting myself because I'm showing myself and other people and my

daughters that like, hey, I thought this way and like life taught me a lesson or I learned something new or I tried something differently. And like, I guess I'm not who I thought it was, but I like who I'm becoming. And there's this Rupi Kaur quote where it's just like, I'm only going to be this version of me today. I want to sit down and get to know her. And I feel like in my like, I'm only going to be this version of me today. I want to sit down and get to know her. And I feel like in my life, I'm just like constantly meeting this next version of myself and introducing her to the world. I love that. That's really, really powerful. Okay. So I want to get like down in the details with this because like, I know a lot of people are going like, yeah, but how do I leave my life? So I want to talk about that. So right now,

we're in this great resignation. A lot of women, particularly women, more women than men are leaving the workforce every single day. There are statistics that say 1,200 women are starting businesses every single day in the US, which I love. And the main incentives to start their own business

is pursuing something that they love, financial freedom and flexibility. So if people are listening and they're like, yeah, those are the reasons I want to leave my job right now. Like I want all those things, but what do I do? Like what the frick do I do as my next step? What would you say to them? So for me, I didn't necessarily know that like my camera would be the vehicle out of the nine to five. I just knew I needed to leave it. So if you are one of those people who you're so burnt out that like the word passion makes your eyes roll because you're like, I don't even know

if I have a hobby at this stage in my life. Like passion, I don't have any time right now. Yes. Particularly women with kids. If only I could have a passion. Yes. So if that's you, what I would actually start with is a not to do list. Do almost like an audit of your calendar and look at the things that you dread, that you hate doing, or the commitments you've made where you're like, I never want to do that again. For example, when I was in my corporate job, I was like, I never want someone to write another year plan for me without asking me what I want. I never want to work in a job where I get 10 days of vacation a year and I have to so thoughtfully use them that I can't even enjoy them. I don't ever want to be in a position where I have to keep my phone on my nightstand because there might be an emergency that requires

me to show up for it. So when you say those three main points of like women wanting to leave, I'm like, yes, I get that. So a non-to-do list is a really great place to start. The other thing that I would say is that sometimes we need people to speak into our lives because we are so close to our own genius that we don't even recognize. Like the things that come so naturally to us are so obvious. And we're like, everyone knows how to do this. Or like, this is so basic knowledge, but turns out that a lot of things that are basic for you are mind blowing for other people. Whether it's a skill you have, a hobby that you're really good at, or a passion that you're like very curious about. I always ask people like, if you're on Google at

two in the morning, like what are you searching for? Or where do you find yourself in the forums, like reading and learning about that? Because that might be an indicator of something that you're passionate about that you can learn about. The next thing that I would say is like, how can you take teeny tiny microscopic action, like inch closer to the vision that you have? There's a story in my book about how when we were struggling to grow our family, I really had to like unpack my grief because I was like holding it inside. I was really angry. And I did this visualization exercise. And your grief was just, you weren't getting pregnant. And then when you did,

I had miscarriages. Yeah. And so it was like after my second miscarriage, I did this exercise. Someone was leading me through this visualization and she was like, picture like the most vibrant version of you. And like, not just picture her, but like slide your fingers into her finger slots, your toes into her toe slots. Like, where are you? What do you see? What do you hear? And like, she had this line and it was like, like a dial on the radio, like turn up your intuition and turn down the noise of the world. In that vision, it was so funny. I remember it so vividly. I was wearing Madewell jeans and a white linen shirt. And as I opened my eyes after the visualization exercise, I like looked down and I'm like,

and here I am in yoga pants and my sweatshirt from high school. And I was like, I don't have all the pieces of that vision. In that vision, I visualized a little girl and pancakes and all of these things that I deeply wanted. But I also recognize that I'm not even buying the jeans that I want to wear in my most vibrant life. Let's take a quick pause to talk about my new favorite all-in-one platform, Kajabi. You know I've been singing their praises lately because they have helped our business run so much smoother and with way less complexity, which I love. Not to mention our team couldn't be happier because now everything is in one place. So it makes collecting data, creating pages, collecting payment, all the things so much simpler. One of our mottos at Boss Babe is simplify to amplify and Kajabi has really helped us do that this year. So of course I needed to share it here with you. It's the perfect time of year to do a bit of spring cleaning in your business, you know, get rid of the complexity and instead really focus on getting

organized and making things as smooth as possible, I definitely recommend Kajabi to all of my clients and students. So if you're listening and haven't checked out Kajabi yet, now is the perfect time to do so because they are offering Boss Babe listeners a 30-day free trial. Go to kajabi.com slash boss babe to claim your 30-day free trial. That's kajabi.com slash boss babe. I your 30 day free trial. That's kajabi.com slash boss babe. I might not be able to like create the child and the pancake breakfast and the Persian rug, but I can go online and buy a pair of jeans and start wearing them to show up a little bit closer to that vision. And it was just this wake up call for me where it was like, you know, you don't have to change zip codes or put in your notice or like do these things to start living your dream life.

But there's probably something so tiny. Like if you want to run a marathon, putting the shoes on. If you want to start a business, doing the research. Like, you know, there's so many ways that we can microscopically move forward. And so that day I ordered a pair of jeans and I was like, I don't have the baby, but I can start showing up a little bit closer to the most vibrant version of myself. And that's step number one. I love that. That actually really speaks to my heart because I think that's something a lot of people can

relate to too. I think we also take for granted that we do these visualization practices too, right? Because if I think back to like 2014, 15, I didn't even know that was the thing you could do. I actually didn't even know about visualization until I got my first coach, which was probably 2017. And she taught me about visualization. I never heard of any personal development stuff. I hadn't heard of The Secret, Tony Robbins, Brenda Rashad, like all the people like who are doing such incredible work in space I don't even know about that and so like even just like giving yourself permission to like visualize and dream

it and it is so so powerful and I remember doing that exact same thing when I had this visualization and I was like wait a minute that's so far from where I'm at right now. Like that's not even possible if I stay here. So hang on a minute. And I think when you have those realizations and don't be scared by that being like, oh, okay. So okay. Got a way to go. Got a little way to go, but what's the next step ordering those jeans or what's the next step researching that business. But I think sometimes people are like, oh yeah, I want to do that. And I'll do that when versus like, there's like a million steps to get to that point. Well, and I was like, am I waiting for the baby to wear the jeans? Like that,

it doesn't work that way. Like what can I control today to help the like uncontrollable come into fruition so that when it arrives, not if it arrives, when it arrives, I am that version of me that is going to be so fully present to the moment. You know, another way I think about it as well is I, cause I, I felt like it's like taking steps, right? Absolutely. And so for me, I use this analogy and it's always stayed with me. If I'm driving from LA to New York, right? If I know I want to drive to New York, first of all, I have to get in the car. Then I have to like start driving, right? And sometimes on this journey, you might feel like partway there, like, oh, I don't know if I can do this. I'm ready to turn around. But when you

realize how far you've come, you're like, well, hang on a minute. It's just as hard to go backwards now. I might as well keep going. And so for me, that was the other thing around like taking action was like, oh, we've taken a bit of action. I'm actually a little bit closer to New York. I'm like, I might still be, I don't know, my geography on the US is really bad. I shot myself in the foot with this one. I might still be in the Midwest.

There you go. Yeah, yeah. Okay, this works. We're on the track. We're on the drive. We're getting there. We realize that we're making progress. That's one thing that a lot of people don't give themselves that allowance for like,

oh, I'm actually making progress. Yes. You know, it's wild to me because a lot of times we let like our procrastination stall us from progress. It's like we want to have all the answers or we want to have the logo and the blog and you know, like we have to have it all figured out before we start. And it's like, no, no, no, no, no. Imperfect action is moving you forward. There's a part of my book where we quote BJ Fogg, and it's like, make your actions so impossibly small that you start. And I think that what has

happened a lot, especially for women, is that we have lost our ability to trust ourselves to follow through. We've tried the juice cleanse. We've tried the diet. We've committed to reading the Bible, like whatever it is. And we've fallen off the path at some point because life happens and we start to doubt ourselves and put ourselves into the shame cycle of like, I said I was going to do this and I didn't like, I can't even trust myself to get myself results anymore. And it's crazy because it's like, we have to build up our beliefs through these tiny little bits of progress. And I think starting small is the most beautiful way you can, because as you start to gain momentum, as you start to get traction, you're building up your belief that

you can figure out what's next. And it's like, we've forgotten that like, what has gotten us this far will carry us forward. You are in a space right now where you are really good at something or an expert at something or curious about something. And we doubt that what has gotten us to where we are can carry us forward. And I think that's the number one reason why we're delaying or saying like, I'm disqualified from going for this thing. And it's like, we're crazy to not see our gifts. Yeah. And sometimes as well, like we can set such big hurdles that then when we don't achieve that cleanse, right. Okay. I'm not just going to like cut chocolate on my diet. I'm going to do this five day cleanse where I barely eat. I eat olives.

And then like you do it, you fail and then you feel shit about yourself versus like, okay, well, if I'm just going to do this, I'm going to cut chocolate for five days. And then like you do it, you fail. And then you feel shit about yourself versus like, okay, well, if I'm just going to do this, I'm going to cut chocolate for five days. And then like you accomplish that. And then you're like, woo, I've got a bit more confidence now to do the next thing. And it like builds on itself. So I totally hear you on like these taking actionable steps

and they don't necessarily have to be huge. It's about, you know, the little incremental parts. But you've been on this journey. What have been some of the major difficulties in like leaving that nine to five or transitioning even your photography into like an online business? Like what were some things that you really like

at some points wanted to give up? Because I feel like we've all had them. And like, we have to be like, something keeps us going. I'm just curious, what for you have been those biggest like hurdles I would say so one of the biggest hurdles was I left a job that had a fancy title to pursue a business and I felt like I had to prove to people that it was important like I remember being like I'm a photographer but like I'm not just a photographer

I shoot 25 weddings yes and I felt like you, when you have these like eight word long titles, executive leader of dah, dah, dah, dah, dah, people just treat you differently versus the identity of entrepreneurship and like people treat your job like a hobby. So that was a really interesting hurdle that I had to let go of that it's not anyone else's job to understand my vision, my business, or my calling. It has to come from me and through me. And I just have to be good with that. The next one was creating these ladders for myself. It's like, I left this five-year plan only to say like, I need to one-up myself constantly. I need to do better. I need to make more. And I remember the day that I made six figures for the first time. I literally remember

like looking in the bank account and being like, boop, it hit. And I was like, I thought this would feel different. I was setting these like arbitrary goals that like, to me proved that like I had made a good bet on myself. I was successful. And I would arrive to the destination and be like, I thought this is going to feel different. And for me, one of the biggest lessons I learned is every time I have pivoted, started something new or had a big breakthrough, it was when I stopped valuing money and started claiming back my time, like treating time as my currency. And when I hit six figures and it felt like crap and I was burnt out to a crisp and I was ready to throw my laptop out the window and be like, I'm never doing this again. I sat down with Drew. He

came home from work and I had this like color-coded plan out. So we need to talk. And I said, I was so much happier when I made $50,000 a year. I said, screw six figures. I don't care about the money. I don't even have time to enjoy the money. Are you with me? Can we go back to living on less so that we have more life? And it was crazy because he actually looked relieved. And it was like we had started our marriage. I was three years into my business and he was living with a shell of who I was. I lived with my computer on my nightstand. I was working all hours of the day. I never disconnected. I traveled with my laptop everywhere. I was always available. And he was like, that sounds amazing. And so when I cut back, which I now have established and coined the term my enough point where I said,

how much do we actually need? We know we can live off of me making 50 grand a year. Let's go back to that. So I cut my workload in half and got back so much time. When I had time again, I became creative again. When I became creative again, I became creative again. When I became creative again, I became curious. When I became curious, I started to learn. And in that quest was when I learned about the online digital course world. If I had just continued on the rat race of six figures, and that's the goal, I would have never gotten back the time that allowed me to go from one to a million. Screw 50,000. Now I'm making millions, not because I was hustling harder,

but because I was working smarter and I was looking at time as my currency. And I can see literal like chasms in my life where there was a before and an after. And it's always when I claim back my time. I think utilizing time as a currency is extremely powerful. So powerful. Because it's so precious. That's one thing we all have in common. We only all have the same amount of time, same amount of hours in a day, the same minutes in an hour. And so what did that look like for you in the sense of like getting curious, like cutting back, but then you were like, oh, I was creative and then curious. What was that process like? Yeah. So I had built a six-figure business in three years flat in an area that I never went

to school in. But it wasn't necessarily because I was the best photographer. There were so many talented photographers in my area. It was because I was really good at business. Define that. What does that mean? So I went to college for business. I learned marketing. I was obsessed with branding, like all of these things. And I recognized that being a photographer meant shooting 5% of the time and being in business 95% of the time. The invoicing, the branding, the blogging, the emails, the pricing guides, like all of these things. I love that you're saying this, by the way, because this is like a lot of the behind the scenes that people don't really get. Yes. Well, and it reminds me of like when I was a kid, I told my mom, I want to be a

veterinarian. My mom was like this bold, brazen woman. And she was like, I'm going to let you job shadow a vet to see if it's what you think it is. I thought it was cuddling puppies. The day I job shadowed a vet, they cut open a turtle, fixed a cat and had to put a bunny down. And I was like, I never want to be a vet. Thank you, mom. I think I'm going to foster puppies. What we think we want and what we think a job looks like is often very different, right? And becoming a photographer, I thought, I get to be behind a lens. I get to create these moments. I get to pose these couples. Guess what? That was the tiniest fragment of what the work I was doing. But what was interesting is that other photographers were taking notice that I went from zero to 100 in my business and they wanted to know how I did it. And it wasn't

anything to do with me being behind the camera. It was me strategically building a business where I knew marketing and branding and all of these other things. And so I had in my slow season, quote unquote, I put up a post on Facebook and said, I'd love to mentor other photographers. Does anyone want to come to my house and I'll teach you how I do what I do? What year was this? This would have been 2014. And within like an hour, like 25 people had like commented on it. And I was charging $200 for a day. And I was teaching them everything. Wow, that's the best $200 someone could have spent in a long time. I know.

I was like, I was giving them everything. Email templates. Like, because I had realized like I built my business while still working my corporate job. So I had systemized things where a lot of creative and artists really struggle with like the management and the system side. And so after a couple of those sessions, I realized I am saying the same thing over and over and over again. Like there are themes that people are struggling with. There are themes in what people need in terms of systems. There

are themes in the resources I'm giving. So then I got curious about like, okay, I wanted to leave the trading time for money and now I'm doing it again in mentorship. How do we make this so that I can do something once and get it to the masses? So I ended up taking this online course and I didn't even want the course itself. I just took it so I could learn how somebody did it.

How do you format it? What systems do you use? Where do you upload it to? I literally just, and I still to this day, take courses just to dissect how somebody's created it. What do I like about it? Where am I getting lost? What is confusing? So I took this course and I told the creator, I'm only going to buy this course if you promise to tell me how you built this. And he said, sure. And that helped me to create my first course, which then I launched it and made $50,000 and almost the rest is history. Do you know what I'm seeing a theme is asking questions. Yes. I think it's really, really powerful because that's how you often find

like you kind of get like kind of coaxed into the areas yeah when you're asking those questions yes and you're looking and you're listening and I definitely can be very guilty of this sometimes I feel like I need to have all the answers on my own I'm like wait let me go and shut myself in my office and come up with all of the answers you do well I've had that I have to not do it I know where it comes from too when I was like a kid like you got sent to your room to like figure out why you're upset and then to come out yeah I know that's why I went to Hoffman yeah I love my parents though but um that was one like a habit that I have and I have to be very intentional and I think sometimes a lot of us

have that where it's like okay I can come can come up with the answers on my own. Versus being out there talking to people, asking people, being inquisitive. Like, hey, how did you do this? Or why did you do that? Or hey, would this help if I gave you this? But then also registering the answers. Because I think sometimes as well, it's sometimes right in front of us. And just when it came um earlier you

were talking about the passion part and you having photography one thing I've really noticed and for someone who had a career obviously in chiropractic was that I felt like how can I possibly transition my skills of chiropractic which are in person yes onto online yeah that doesn't make any sense there's nothing but what I realized was actually there's so much crossover, like so much crossover and so many transitional skills. And I think the reassurance that a lot of people need to hear is, yeah, you might be leaving a career path that you thought you were on, but you have so many skill sets. Like we literally had Miss Excel on the podcast, like not that long ago. She's like literally built her business now, teaching people how to use Excel spreadsheets. And like the point is like realizing that we have so many skill sets and

those skill sets might look different from someone you're following and for yours or to mine, or you might even be still figuring out those skill sets. But the number one thing is like you're trying and you're putting it out there. Like, Hey, does someone need to know this thing? What you just said, like we have to talk about this, putting it out there. And there's a chapter in my book all about this woman named Kathy, who was like my office mate. I was late at work. I had this desire to start this photography business. We had a color printer at work. So I created a vision board in Microsoft Word because it was pre-Pinterest days. I laid out all these pictures of like wedding photos, printed it off on the color printer, wanted to laminate it, get it stuck in the laminator. And I am like ripping it out

because no one at my corporate job knew that I wanted to be a photographer. I had kept it very separate. I didn't want to give them any inclination that I wanted out. So the next day I have to show up to work and I like tell Kathy like, I think I'm at a jam to the laminator. And there's like a piece of paper that says photos by Jenna Lee in there. And that was my first business name. And I was so embarrassed. And I was like, either she's going to like go tell my boss that I'm trying to get out or she's going to like understand. And so I was like, yeah, I haven't really ever told anyone this, but like I really love photography. And I have these dreams of being a photographer. And her eyes like lit up and she was like, I love scrapbooking.

And I should have been able to tell this because she made the most epic bulletin boards ever at work. But it was fascinating when I finally spoke the dream and shared it with someone, even if it was just Kathy, where I was like, oh, I no longer feel like I'm riding two Clydesdale horses going in opposite directions. I now am saying it. So when you said, I'm willing to try something and share it, I think that's a huge challenge for people because we often say like, oh, when I have the audience, I'll start talking about this thing. Or when I have the website to reveal, I'll start talking about it. But there is going to be no one ready for you to launch to if you don't start building up the interest or the curiosity just by sharing the things

that you're good at, that you're passionate about. That's why I love when you share how you make your morning beverages or a new vitamin you're taking or things like that because I'm so curious. It makes sense. You're passionate about it. You're not monetizing that right now. But now if you ever decided to, I'd be like, that makes total sense. And when it comes to sharing our passions or our curiosities, we often keep them so close to our hearts that then all of a sudden, if we want to do this grand reveal of like, hey, I'm going in a different direction, people would be like, wait, what? I'm so confused. And so when we start to like leak that like, oh, I'm really good at this thing, or I'm curious about this thing, or a lot of people ask me

about this thing, I'm just going to share it with you. I don't have any like big plan or, you know, big funnel to throw you into, but I just want to start sharing it. You start to build up your confidence and you start to see what resonates. And I think that can be a huge first step. 100% like sharing it, putting it out there, speaking it into existence, obsessed. I fully agree. I'm also like hearing, which is just really interesting is like, sometimes we hold ourselves accountable to something we've said and we think others are holding us accountable to it, but they're actually not. Like I was just realizing this, like, hang on a minute. Like you sometimes don't want to put it out there because you think that someone's going to be like judging you if you don't do it, but it's you who's judging you. But actually when you overcome that and you put it out there, I just

think sometimes we take life too seriously. My Facebook statuses from like a decade ago remind me of how I was like, Hey, I got a new camera. Would anyone like to model for me? And like things like that where I'm like, hell yeah, 23-year-old Jenna, you put yourself out there. And it's crazy because I look back and I'm like, no one was going to be my own publicist. No one's going to be out there like marketing my dreams for myself. I was bold. I saw a status the other day from literally a decade ago and it was like, photos by Jenna Lee has 300 fans on Facebook. Let's celebrate. And like three people liked it. But I was like constantly like nudging people and reminding people like,

I'm going for this. I'm doing this. I'm available for this. And I think nowadays we're so used to this like curated perfection that we want to wait to even start sharing those ideas. Yeah. Do you know what I've started sharing? This is like so vulnerable, you guys. And I always want to, the reason I feel so passionate about the podcast, by the way,

is like I really feel like it gets like the real behind the scenes and the real stories. And, you know, I never want people to think, oh yeah, like Daniel has everything figured out. I absolutely do not. And so one thing I've like started sharing is like, I absolutely love interviewing people. Like I love asking, basically I get an excuse to be nosy, but I kind of love asking all these questions. And I just started like putting it out there. I was like, I want to be the next Ellen DeGeneres.

I love that. There's a gap in the system. I'm like even blushing saying it, but it's like, if I don't say it and if I don't speak it, then like it will never happen. Whereas I'm like, if I put it out there, someone might be listening and be like, oh yeah don't say it and if I don't speak it, then like it will never happen. Whereas if I put it out there, someone might be listening and be like, oh yeah, like you should do this. Can I give you some feedback on this?

You are already doing an incredible job because before we started this interview, you said, who is your favorite interviewer and why? So you are much better than you give yourself credit for. Instead of going into your room, you're asking the questions. When you're saying these things, and so if you're like embodying the spirit of like just getting better at what you're already doing, regardless of where you land. Yeah, exactly. I just want to share that is because like, it's so vulnerable for me, yet I do it anyway. Like, no, like I want to do this. So I need to put it out there. I need to

be brave and speak it into existence because I'll never happen if I keep it close to my chest and yeah and this is also coming from someone whose instinct is to totally go away in their office and figure it out but I've learned like that doesn't get me anywhere so like I learn and sometimes I'll literally go you know back to my old ways I'm like oh hang on a minute why am I trying to figure this out why am I not just telling people what my challenge is that I'm trying to overcome and that doesn't necessarily need to be my dreams. It might just be a problem at work where I'm like, wait, this is my KPI, but I cannot figure for the life of me how to like solve this problem right now. So I need to like share it because I'm also a brainstormer. And my brain works much better when I brainstorm with people.

Do you want to know what my vision is? I would love to know. I've never told anyone. Oh my God, is this an exclusive? It very much is. I want to write more books. I do, but you said you never wanted to be an author. I said I never wanted to be an author at all. And I...

I'll let you change your mind. I changed my mind and I loved the process. I loved every bit of it. And people hate the process of writing books. Yeah, they do. I loved every part of it from the creative to the editing, to the writing, to the re-editing, to the re of writing books. Yeah, they do. I loved every part of it from the creative to the editing, to the writing, to the re-editing, to the re-editing. I've loved every part of it so much. Whereas like if we can live in the woods and I can write and run my podcast,

that is my dream life. And that's it. Wow. I'm so happy for you. Isn't that wild? Such an amazing realization. And I think that just like brings us full loop so nicely because we literally started this conversation around like feeling like changing your mind and whether sometimes you feel guilty about that. But having preconceived ideas about something good, some turn out better than you thought it was. Like that book one, you're like,

I don't want to write a book. Okay, I'll write a book. Oh my God, I love writing a book. Or hang on a minute, I want to be a chiropractor. Oh, I like it. Oh no, I don't like it. I want to leave. Like, it's okay.

We get to change our mind in all the directions because like, why are we here otherwise? That's what I always think. Why am I here if I'm not enjoying it? And it's so easy to get wrapped up in the materialistic things. But at the end of the day, they mean absolutely jack shit.

As long as you can like truly and you have a roof over your head, like yeah, you're better than most. Isn't there a statistic that says like once you're earning $70,000, the threshold of happiness is diminished. Yeah. It just is like,

you don't buy you anymore happiness. So I think that's a really important thing to remember. Yeah. Well, and that's the thing too, is it's like we live in this culture of more, more, more. And I've actually cut back a lot over the last few years. I'm in this season of life where my kids are little and they're only going to be little for so long. And I've really welcomed

the slowdown intentionally in trusting that I can pump the brakes and I still know how to push the gas pedal if and when I'm ready to. A lot of women doubt their ability to do that. And I feel like they stay stuck because they believe the lie of momentum. Momentum is a powerful thing, but you can also generate momentum again, right? Like you got going once, you got the ball rolling, like you can slow it down a little bit and it's going to be okay. And I think we worry like, if I slow down, am I going to be irrelevant? Am I not going to be able to get started again? Are people going to forget about me? Am I going to miss my big break if I say no to things? And it's like, we're constantly saying yes to things, doubting and forgetting again, what has gotten us here will

carry us forward. And so it's a beautiful place to be in that, like I'm honoring the slowdown and welcoming it, even though I'm still doing really big things, they just look different. And it's like, again, just another version of who I am. Yeah. Welcoming the slowdown. And we were talking about the power of seasons and recognizing that just seasons change. They come and they go, they transition and it's part of life and I think that's also really been powerful for me around like oh seasons of hustle and seasons of breathing and listening to my body and seasons of you know preparing to blossom and then seasons of oh okay like I want to scale back now and that's for me has been like the biggest realization in the sense

of like life changes and yes maybe my life isn't exactly how I thought it would be but that's also okay I don't necessarily need the the book that was perhaps showed to me as a yeah yeah as a child oh this is what your life looks like and that's what success looks like yeah it doesn't well intentioned thoughts that permeated into us in a way that doesn't have us asking, what does this feel like? I think we're so focused on what do things look like. How does it feel? Yeah, exactly.

So I want to talk a little bit more about the book. Yeah. Because I really also want to ask you, you said you didn't want to be an author, and yet you ended up writing this book. To me, that says you had a, there was a strong why. The why was probably bigger than you because a, there was a strong why. The why was probably bigger than you because you didn't want to write it. So why did you write it?

For so long, especially in the digital course world, I thought about the trade-off of time and money, right? I was like, why would anyone spend two years writing a book when you could launch a new course, get it out into the world and make the same amount of money in two months. I just could never wrap my brain around it, especially as a digital creator where you can have an idea, record it, put it out, get feedback and make money on it. It was like, I don't understand why anyone would put themselves through it. And there's this really great story in the epilogue at the end of the book. It is like my favorite part of the book. Oh, it's the final pages. And it was how I went to this massage therapist during COVID. So it's

when things were finally like creeping open, she was actually like an intuitive healer beyond being a massage therapist. And she does my massage. And at the end of it, she's like, can I tell you what came up for you today? And I was like, yes, please. And she was like, there's a project that you know you have to do, but you're avoiding it. I wanted to force your hips down because you are trying to steer away from it and around it, but you know what it is. And the moment she said that, I was like, it's a book. And I knew it. Like I knew it so innately, like where for so long, I was like, no, no, no, no, no, no. It's such an ego move.

Why does anyone do it? It's such a long process. And I literally came home from that massage with like the chair, you know, like the table marks on my face. And Drew was like, how was it? And I was like, I have to write a book. He's like, wait, you make a massage?

Yes, he's like, I don't. And I, it was crazy to me how one person, a stranger who I met named Thea, became like my permission grantor. She didn't even tell me what it was, I knew. And it reminds me how many people are walking through their life just waiting for someone to say to them,

there is something you need to do and you know what it is, now go do it. And it was so clear to me in that moment. And it was in a season where we were thinking about trying to get pregnant for our second baby. And I was like, all right, I'm going to get going on this thing. Like I literally opened up a doc that day and started writing and it like poured out of me. And it's crazy because I've never worked harder on anything. And like the book world is super old school. You don't make a ton of money. It's really long and complicated. There are so many different steps in the process and I love it. And I'm so excited about it. And I'm like doing everything in a way that feels so

aligned to my mission and the mission of the pages. And it's crazy, but it just reminds me of like, she literally could have said that to every single person who came in for a massage and about every single person who would walk out and say, oh yeah, I need to do this thing, whatever that thing is. So powerful. And I think as well, like whether you believe in that or not, it's like just the message alone was just incredible. And what do you feel if the woman picks this up? You know, she's like browsing the bookstore or she's seeing this online. And what would you say is the biggest takeaway she's going to get from this? It's not a book that gives you

a step-by-step process on how I did things. It's a book that gets you back home to yourself so that you can listen on how you need to do things. And so it's not about my truth or my stories. It's about coming back to your truth, your voice, your stories. It's like the dials on the stereo, turning your intuition back up so that you can build a life that feels good, a life that you don't have to fake to enjoy any longer. And also I will say like with the stories that are in there, I think what's really powerful is they're kind of stories that a lot of women will have experienced. That was my biggest thing. I was like, oh, I've had this similar situation. And so even though the stories are there, you've written it in such a way that was like, oh, hang on a minute. Like I could literally be Jenna in this

book right now. Yes. It's weird because I kept the project so close to my heart. Like even my husband didn't read it until recently. And there's, you know, there's a lot of vulnerable things. Like I've been online for a decade, but there's, I mean, the whole book is things I've never shared. And, you know, it spans from things like career to body image, to relationship, to friendship. And it's like all of the conversations we're having behind closed doors that we're afraid to like whisper into the like light that's inside. I'm really proud of it. should be it's amazing and also for me like I love reading in the sense of like Natalie is like literally a book yeah I'm like she'll read all the time I'm like yeah whereas I like books that are really practical and what I loved about yours was

like there was like even at the end of like chapter one you were already like I could add things in that I could write about oh yeah like this is a great question to ask me. There's tools. Yeah, so it felt like I was actually doing something by reading the book versus just like reading it and then like going away. I was like, oh, there's some like really practical tips in here.

Anyone who is that, has a little bit of an ambitious boss babe inside is going to absolutely love the book. So I appreciate you. Where can they find more information? Like I know we're going to put links in the descriptions, but do you want to share some here too? Yeah. Howareyoureallybook.com. So the title is How Are You Really? And it is the difference in a conversation with others or with yourself where you get past the good and the

busy and the fine and you lean into how you're really doing. And so it's howareyoureallybook.com and then jennacutcher.com will lead you to all of the places from the Gold Digger podcast to Instagram to everything and cute pictures of my little girls. They are really, really cute. Like the cutest. I can totally see that. And now, yeah, you've got the dream. Wait, I need to ask a very important question. Do you still have your Madewell jeans and your linen white t-shirt? I absolutely do. I'm wearing my linen dress today. Drew laughs at me because in the book, I share the vision and it had to do with pancakes.

And every Saturday, we have pancakes and he'll look at me and I'll have just misty eyes every Saturday. I like get misty just thinking about it. And he'll look at me and it's like, we're living it. Like we're literally living it. It's the most beautiful thing. Oh my God, you are. She's getting upset.

We're going to round out. We're going to round out now before the tears start flowing. Because I know you miss them right now. But thank you for coming on. And thank you for like always being open. Like if that's one thing about you and what you've done, you've opened up a lot of conversations for a lot of women. I really appreciate that.

Thank you for having me. Thank you so much for listening. And if you enjoyed this episode on the Boss Babe podcast, then I'd absolutely love it if you leave us a review. As a thank you, we'll send you our Side Hustle Success Kit,

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